Playboy’s famous first cover featuring Marilyn Monroe has since gone viral following the news of Hef’s death.

Although often confused – seeing as Hefner bought the plot next to Marilyn Monroe burial place – as acquaintances, the two never actually met.

PA

Starting out from his Hyde Park kitchen in 1953, Hefner would go on to take Playboy to unparalleled heights.

Throughout the 60s and 70s, he employed an editorial staff that conducted and produced long-form interviews and features with everyone from Marlon Brando to Martin Luther King.

Speaking to Piers Morgan in 2011, he said:

She was actually in my brother’s acting class in New York.

But the reality is that I never met her. I talked to her once on the phone, but I never met her.

She was gone, sadly, before I came out here.

A picture wrongly believed to be Hefner lighting a cigarette for Monroe is in fact British thespian Laurence Olivier with the Hollywood icon at a press conference for their 1957 flick The Prince and the Showgirl.

Furthermore, the iconic pictures printed in that first Playboy centrefold were not specifically taken for the magazine.

The nude shot of Monroe, then just a struggling Norma Jean Baker trying to make it as an actress, was taken for a calendar in 1949.

The cover was cropped from a public appearance Monroe made in New Jersey for the Miss America Pageant.

Playboy

PA

Despite this, she has become almost synonymous with the Playboy brand.

Speaking about her legacy in 2012, Hef said:

I would have loved to [have dated Monroe]. I’m a sucker for blondes and she is the ultimate blonde.

His favourite movie of hers was ‘without question’ Some Like it Hot as it was ‘at the end of her career and it indicated how much real talent she had.’

He added:

She died young and remains beautiful in all our minds. She is without question the definitive sex icon of our time.

There’s something unique when an iconic legendary figure is more famous 50 years after her death than at the height of her career.

PA

Hefner played a huge part in the sexual revolution, making nudity acceptable in mainstream publications and high society.

His magazine covered and championed the black artists and politicians prior to the civil rights act, famously profiling Miles Davis in 1962.

Presidential historian Douglas Brinkley spoke positively of the leaps and bounds Hefner made in the early days of Playboy, telling CNN:

He’s a giant of American journalism. He really changed things in the 1950s and 60s, not just with having an open discussion about sexuality but bringing in Playboy magazine extraordinary, edgy interviews with people ranging from novelists Jack Kerouac to Kurt Vonnegut, Joseph Heller…

It became almost a must-read in many ways. Some years ago, he invited me to visit him in the Playboy mansion, because as a historian he wanted me to see his archive. He had giant scrapbooks, he had saved everything his entire life.

He was particularly proud in his role in civil rights. He fought against Jim Crow in the South. He integrated the Playboy clubs in Miami and New Orleans.

Hefner is survived by his widow Crystal Harris and his four children from separate marriages.